Studies on L-Ascorbic Acid Derivatives. III. Bis (L-ascorbic acid-3, 3') phosphate and L-Ascorbic Acid 2-Phosphate

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Phosphorylation of 5, 6-isopropylidene-L-ascorbic acid (I) in acetone with phosphoryl chloride gave, in addition to L-ascorbic acid 3-phosphate (II) and 3-pyrophosphate (III), the following two derivatives, i.e., bis (L-ascorbic acid-3, 3') phosphate (IV) and L-ascorbic acid 2-phosphate (V). The structure of these phosphates was determined on the basis of elemental analysis, potentiometric titration, NMR-analysis, supplemented by studies of the hydrolysis. IV was hydrolyzed by acid and alkali most readily among the four isomers. By being passed through a column of Dowex-1-chloride with 1N hydrochloric acid, this compound quantitatively afforded equimolar amount of II and L-ascorbic acid. On the other hand, during the hydrolysis of V in 0.5N hydrochloric acid at 100°, the phosphoryl migration to II was ob served. On the alkali treatment, V was shown to be stable and no migration was detected.

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